Are We On A Date? (Pt 1) / by Ben Weston

I was waiting for her at the bar and still wasn’t sure if it was a date.

[phone vibrates]

“I’m so sorry to be late to our first business meeting.”

Ok, so maybe it’s not a date.

After hanging out for about 20 minutes she says, “You know, when I first met you, I thought you were too charming to have any substance.”

Thank you!

Wait...that’s flirting, right? So it’s a date now?


I’ve recently been having private conversations with men around the Aziz Ansari news and #MeToo movement.

One thing that keeps coming up is feeling like you either can’t or it's unclear how to express your desires with women.

I get it. Expressing your desires is vulnerable and scary but you still want to be masculine and assertive, all the while not crossing any boundaries.

The problem is, I feel like the current models of behavior for men don’t do the job.

We have romantic comedies where the hero is a guy that keeps pursuing his love interest in spite of her numerous attempts to tell him “no”. Eventually she relents, says yes, and realizes he’s the man of her dreams.

(Why John Cusak, why?)

And then we have the pick up artist world where one of the first things you're taught is literally how to give a backhanded compliment to a woman -- a “neg” -- meant to show that you’re the kind of guy that’s NOT interested in her.

Good lord.

Keep pursuing her in spite of her repeated and clear “no” or pretend that you’re not interested in her?

Bob, I’ll choose what’s behind door #3, please.


As our “business meeting” progressed it felt like we were flirting and hitting it off but I still wasn’t sure where she was at.

Maybe she was just naturally flirty but didn’t mean anything from it?

I honestly had no clue.

After she finished sharing a story, I told her: “I have to confess - I’m having some difficulty focusing on what you’re saying because I’m finding myself really attracted to you.”

Without any hesitation, she responds with: “Oh, I know. But before you kiss me...”

Now, at the time of writing this, I’ve already spent several minutes desperately trying to remember what she said after that but I think in my excitement over her saying the words “kiss me” I zoned out a bit.


But I remember the gist of the message: wait.

We left to try to find dinner, finally locating a BBQ joint still serving food at that hour.

At some point after our pulled pork sandwich and fish tacos arrived she turned to me and asked, “May I kiss you?”

“Sweet Jesus, yes please!” is what I thought in my head.

I am 100% positive that I looked waaaaaay cooler giving a deep, manly “Yes” and leaning in.

(Damn, I really hope so)

Sure, that whole evolution from telling her I was attracted to her and her eventually asking to kiss me looks nothing like a typical romantic comedy setup or what pickup artists teach.

But damn, it’s just so much *easier* being upfront. I don’t want to be constantly guessing.

Plus, I find it extremely sexy when a woman is that direct with what she wants.

[Update: click here to find out what she had to say about the evening]